Polyesters are heterochain macromolecular compounds that contain carboxylic ester linkages in the chain as opposed to other polymers containing ester groups which are pendant from the chain such as poly (acrylates) and poly(vinyl esters). Polyesters can be made from (1) the reaction of diols with dicarboxylic acids, by (2) the intermolecular polymerization of hydroxycarboxylic acids and by (3) ring-opening polymerizations of lactone and cyclic esters. The first produces an AABB type polyester while the latter two produce the AB type polymer. Catalysts used in direct esterification reactions as in the above, when needed to maintain the self-catalyzed reaction, are sulfonic acids, e.g., toluenesulfonic, phosphoric acid and dialkyltin oxides. Strongly acidic catalysts, however, tend to discolor the product and must be removed from it. Instead of the above reactants which contain carboxylic or dicarboxylic acid groups, similar compounds in which carbonyl or dicarbonyl chlorides replace the carboxylic acid groups can also be used to react with the hydroxyl groups. The by-product is hydrogen chloride. Transesterification of diesters of monohydric alcohols with dihydric alcohols is yet another method of obtaining the polyesters.
In the use of carbonyl chlorides the by-product acid must be absorbed and disposed of while the monohydric alcohol by-product in the transesterification reaction must be removed or poor yields or low molecular weight polyester may result.
Polyamides are normally thought of as condensation products formed by the intramolecular reaction of difunctional amino acids or between dibasic acids and diamines. The former reaction produces an AB-type polymer and the latter an AABB-type. The polyamides are frequently referred to generically as nylons. Polyamides can also be prepared by the addition of an amine to an activated double bond, e.g. an unsaturated amide. Diamines can also be reacted with diamides to give polyamides. The use of diacid chlorides in place of the dicarboxylic acids to react with the diamine is another route to polyamides. Yet another method of preparing the polyamides is by the reaction of diacids with diisocyanates. The by-products of these latter methods is an acid or salt which generates a disposal problem. Also involved is the handling of toxic materials in the case of using diisocyanates.
It has now been found that polyesters and polyamides can be made without the corrosive HCl or undesirable monohydric alcohols as by-products of the polyester reaction or without the by-product acid or salt or the handling of the toxic reactants in the polyamide reaction. The polyesters and polyamides can now be made by reacting a bis(trichloromethylketone) compound with a dihydric alcohol and a diamine, respectively.
Thus, for example, a bisphenol can be reacted with bis(trichloroacetyl)phenyl ether in the presence of a basic catalyst to obtain a polyester.
Polyketones can also be made by the process of this invention by reacting the bis(trihaloacetyl)aromatic compounds with bis(acyl)aromatic compounds to form the polyketones. The polyketones made thereby are poly-.beta.-diketones, products not heretofore made, and, thus, new compounds. No reference to such polymers has been found in the literature.